2β,4a,7-trihydroxy-1-methyl-8-methylene-gibb-3-ene-1α,10β-dicarboxylic acid 10,10'-anhydride 1->4a;1'->4'a-dilactone
A
GA3-7-alkohol
B
(3S,3aS,4S,4aS,6S,8aR,8bR,11S)-6,11-dihydroxy-3-methyl-12-methylene-2-oxo-4a,6-ethano-3,8b-prop-1-enoperhydroindeno[1,2-b]furan-4-carboxylic acid
Conditions | Yield |
---|---|
With sodium tetrahydroborate; acetic acid In tetrahydrofuran for 0.5h; Yield given; | A 72% B n/a |
With sodium tetrahydroborate; acetic acid In tetrahydrofuran for 0.5h; other conditions; Yields of byproduct given; | A 72% B n/a |
gibberellin A3-ketone
(3S,3aS,4S,4aS,6S,8aR,8bR,11S)-6,11-dihydroxy-3-methyl-12-methylene-2-oxo-4a,6-ethano-3,8b-prop-1-enoperhydroindeno[1,2-b]furan-4-carboxylic acid
Conditions | Yield |
---|---|
With potassium dihydrogenphosphate; potassium tri-sec-butyl-borohydride |
Diacetyl-gibberellinsaeure
(3S,3aS,4S,4aS,6S,8aR,8bR,11S)-6,11-dihydroxy-3-methyl-12-methylene-2-oxo-4a,6-ethano-3,8b-prop-1-enoperhydroindeno[1,2-b]furan-4-carboxylic acid
Conditions | Yield |
---|---|
With sodium methylate In N,N-dimethyl-formamide at 23℃; for 4h; |
gibberellin A5
(3S,3aS,4S,4aS,6S,8aR,8bR,11S)-6,11-dihydroxy-3-methyl-12-methylene-2-oxo-4a,6-ethano-3,8b-prop-1-enoperhydroindeno[1,2-b]furan-4-carboxylic acid
Conditions | Yield |
---|---|
With air; alpha-ketoglute dipotassium; potassium ascorbate; iron(II) sulfate In various solvent(s) at 30℃; for 2h; enzyme preparation from anthers of Oryza sativa L., pH 8.0; Yield given; |
ent-7α-hydroxykaurene
(3S,3aS,4S,4aS,6S,8aR,8bR,11S)-6,11-dihydroxy-3-methyl-12-methylene-2-oxo-4a,6-ethano-3,8b-prop-1-enoperhydroindeno[1,2-b]furan-4-carboxylic acid
Conditions | Yield |
---|---|
With Giberella fujikuroi at 25℃; for 24h; incubation; |
0(3),0(13)-Diacetyl-gibberellin-A3-7-aldehyd
(3S,3aS,4S,4aS,6S,8aR,8bR,11S)-6,11-dihydroxy-3-methyl-12-methylene-2-oxo-4a,6-ethano-3,8b-prop-1-enoperhydroindeno[1,2-b]furan-4-carboxylic acid
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: PDC / dimethylformamide / 3.5 h / 23 °C 2: NaOCH3 / dimethylformamide / 4 h / 23 °C View Scheme |
(3S,3aS,4S,4aS,6S,8aR,8bR,11S)-6,11-dihydroxy-3-methyl-12-methylene-2-oxo-4a,6-ethano-3,8b-prop-1-enoperhydroindeno[1,2-b]furan-4-carboxylic acid
A
allogibberic acid
B
(4bR,7S,9aS,10R)-7-hydroxy-1-methyl-8-methylene-4b,6,7,8,9,10-hexahydro-5H-7,9a-methanobenzo[a]azulene-10-carboxylic acid
Conditions | Yield |
---|---|
With sodium carbonate at 240℃; Product distribution; 1-5 min; | A n/a B 100% |
With sodium carbonate at 240℃; 1-5 min; | A n/a B 100% |
With hydrazine |
acetic anhydride
(3S,3aS,4S,4aS,6S,8aR,8bR,11S)-6,11-dihydroxy-3-methyl-12-methylene-2-oxo-4a,6-ethano-3,8b-prop-1-enoperhydroindeno[1,2-b]furan-4-carboxylic acid
Diacetyl-gibberellinsaeure
Conditions | Yield |
---|---|
With pyridine; dmap for 12h; Cooling with ice; Inert atmosphere; | 99% |
With pyridine Ambient temperature; | 2.0 g |
5-Hexen-1-ol
(3S,3aS,4S,4aS,6S,8aR,8bR,11S)-6,11-dihydroxy-3-methyl-12-methylene-2-oxo-4a,6-ethano-3,8b-prop-1-enoperhydroindeno[1,2-b]furan-4-carboxylic acid
Conditions | Yield |
---|---|
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 16h; Inert atmosphere; | 99% |
(3S,3aS,4S,4aS,6S,8aR,8bR,11S)-6,11-dihydroxy-3-methyl-12-methylene-2-oxo-4a,6-ethano-3,8b-prop-1-enoperhydroindeno[1,2-b]furan-4-carboxylic acid
methyl iodide
gibberellic acid methyl ester
Conditions | Yield |
---|---|
With potassium carbonate In acetone | 98% |
With potassium carbonate In acetone at 20℃; Inert atmosphere; | 95.4% |
With potassium carbonate In acetone at 18℃; for 20h; | 94% |
With potassium carbonate In acetone | 92% |
With cesium fluoride In N,N-dimethyl-formamide for 24h; Ambient temperature; | 407 mg |
(3S,3aS,4S,4aS,6S,8aR,8bR,11S)-6,11-dihydroxy-3-methyl-12-methylene-2-oxo-4a,6-ethano-3,8b-prop-1-enoperhydroindeno[1,2-b]furan-4-carboxylic acid
dimethyl sulfate
gibberellic acid methyl ester
Conditions | Yield |
---|---|
With potassium carbonate In acetone | 97% |
(3S,3aS,4S,4aS,6S,8aR,8bR,11S)-6,11-dihydroxy-3-methyl-12-methylene-2-oxo-4a,6-ethano-3,8b-prop-1-enoperhydroindeno[1,2-b]furan-4-carboxylic acid
ent-3α,13-dihydroxy-20-norgibberella-1(10),16-diene-7,19-dioic acid
Conditions | Yield |
---|---|
With lithium; lithium diisopropyl amide In tetrahydrofuran; ammonia at -78℃; | 95% |
(3S,3aS,4S,4aS,6S,8aR,8bR,11S)-6,11-dihydroxy-3-methyl-12-methylene-2-oxo-4a,6-ethano-3,8b-prop-1-enoperhydroindeno[1,2-b]furan-4-carboxylic acid
C19H24O5
Conditions | Yield |
---|---|
With lithium In ethanol; ammonia at -78℃; | 93% |
(3S,3aS,4S,4aS,6S,8aR,8bR,11S)-6,11-dihydroxy-3-methyl-12-methylene-2-oxo-4a,6-ethano-3,8b-prop-1-enoperhydroindeno[1,2-b]furan-4-carboxylic acid
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 60℃; | 93% |
benzyl chloride
(3S,3aS,4S,4aS,6S,8aR,8bR,11S)-6,11-dihydroxy-3-methyl-12-methylene-2-oxo-4a,6-ethano-3,8b-prop-1-enoperhydroindeno[1,2-b]furan-4-carboxylic acid
C26H28O6
Conditions | Yield |
---|---|
With potassium carbonate In acetone | 92% |
acetic anhydride
(3S,3aS,4S,4aS,6S,8aR,8bR,11S)-6,11-dihydroxy-3-methyl-12-methylene-2-oxo-4a,6-ethano-3,8b-prop-1-enoperhydroindeno[1,2-b]furan-4-carboxylic acid
Conditions | Yield |
---|---|
With pyridine; dmap at 20℃; | 91% |
ethyldimethylsilyl chloride
(3S,3aS,4S,4aS,6S,8aR,8bR,11S)-6,11-dihydroxy-3-methyl-12-methylene-2-oxo-4a,6-ethano-3,8b-prop-1-enoperhydroindeno[1,2-b]furan-4-carboxylic acid
Conditions | Yield |
---|---|
With 1H-imidazole In dichloromethane at 0 - 25℃; Inert atmosphere; | 89% |
(3S,3aS,4S,4aS,6S,8aR,8bR,11S)-6,11-dihydroxy-3-methyl-12-methylene-2-oxo-4a,6-ethano-3,8b-prop-1-enoperhydroindeno[1,2-b]furan-4-carboxylic acid
n-hexadecanoyl chloride
Conditions | Yield |
---|---|
With pyridine for 15h; Ambient temperature; | 83% |
triethylsilyl chloride
(3S,3aS,4S,4aS,6S,8aR,8bR,11S)-6,11-dihydroxy-3-methyl-12-methylene-2-oxo-4a,6-ethano-3,8b-prop-1-enoperhydroindeno[1,2-b]furan-4-carboxylic acid
Conditions | Yield |
---|---|
With 1H-imidazole In dichloromethane at 0 - 25℃; Inert atmosphere; | 81% |
(3S,3aS,4S,4aS,6S,8aR,8bR,11S)-6,11-dihydroxy-3-methyl-12-methylene-2-oxo-4a,6-ethano-3,8b-prop-1-enoperhydroindeno[1,2-b]furan-4-carboxylic acid
(4bR,7S,9aS,10R)-7-hydroxy-1-methyl-8-methylene-4b,6,7,8,9,10-hexahydro-5H-7,9a-methanobenzo[a]azulene-10-carboxylic acid
Conditions | Yield |
---|---|
With hydrogenchloride In water for 3h; Heating; | 78% |
at 250 - 300℃; Product distribution; |
(3S,3aS,4S,4aS,6S,8aR,8bR,11S)-6,11-dihydroxy-3-methyl-12-methylene-2-oxo-4a,6-ethano-3,8b-prop-1-enoperhydroindeno[1,2-b]furan-4-carboxylic acid
C19H21IO6
Conditions | Yield |
---|---|
With Iodine monochloride; sodium hydrogencarbonate In acetonitrile for 5h; Ambient temperature; | 77% |
(3S,3aS,4S,4aS,6S,8aR,8bR,11S)-6,11-dihydroxy-3-methyl-12-methylene-2-oxo-4a,6-ethano-3,8b-prop-1-enoperhydroindeno[1,2-b]furan-4-carboxylic acid
Conditions | Yield |
---|---|
With water; sodium hydroxide for 1.5h; | 77% |
With tris(pentafluorophenyl)borate; benzo[1,3,2]dioxaborole In dichloromethane at 25℃; for 24h; Reagent/catalyst; |
(3S,3aS,4S,4aS,6S,8aR,8bR,11S)-6,11-dihydroxy-3-methyl-12-methylene-2-oxo-4a,6-ethano-3,8b-prop-1-enoperhydroindeno[1,2-b]furan-4-carboxylic acid
(4bS,7S,9aS,10R)-1,7-dimethyl-8-oxo-4b,6,7,8,9,10-hexahydro-5H-7,9a-methanobenzo[a]azulene-10-carboxylic acid
Conditions | Yield |
---|---|
With hydrogenchloride In water at 100℃; for 3h; Wagner-Meerwein Rearrangement; | 76.5% |
With hydrogenchloride | |
Multi-step reaction with 2 steps 1: aqueous HCl 2: HCl View Scheme | |
With hydrogenchloride In water for 2h; Reflux; |
(3S,3aS,4S,4aS,6S,8aR,8bR,11S)-6,11-dihydroxy-3-methyl-12-methylene-2-oxo-4a,6-ethano-3,8b-prop-1-enoperhydroindeno[1,2-b]furan-4-carboxylic acid
Conditions | Yield |
---|---|
With hydrogenchloride; water at 60℃; | 75% |
With hydrogenchloride at 50℃; |
(3S,3aS,4S,4aS,6S,8aR,8bR,11S)-6,11-dihydroxy-3-methyl-12-methylene-2-oxo-4a,6-ethano-3,8b-prop-1-enoperhydroindeno[1,2-b]furan-4-carboxylic acid
2,3,4-tri-O-acetyl-α-L-arabinopyranosyl bromide
Conditions | Yield |
---|---|
With Celite; silver carbonate In dichloromethane Heating; | 75% |
(3S,3aS,4S,4aS,6S,8aR,8bR,11S)-6,11-dihydroxy-3-methyl-12-methylene-2-oxo-4a,6-ethano-3,8b-prop-1-enoperhydroindeno[1,2-b]furan-4-carboxylic acid
A
GA3-7-alkohol
B
C32H44N2O6
Conditions | Yield |
---|---|
With sodium tetrahydroborate; dicyclohexyl-carbodiimide In tetrahydrofuran; 1,4-dioxane 1.) -15 deg C, 2.) 5 deg C, 12 h; | A 74% B 3% |
(3S,3aS,4S,4aS,6S,8aR,8bR,11S)-6,11-dihydroxy-3-methyl-12-methylene-2-oxo-4a,6-ethano-3,8b-prop-1-enoperhydroindeno[1,2-b]furan-4-carboxylic acid
(S)-oxiranemethanol
Conditions | Yield |
---|---|
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0 - 20℃; for 6h; | 71% |
(3S,3aS,4S,4aS,6S,8aR,8bR,11S)-6,11-dihydroxy-3-methyl-12-methylene-2-oxo-4a,6-ethano-3,8b-prop-1-enoperhydroindeno[1,2-b]furan-4-carboxylic acid
C19H24O7
Conditions | Yield |
---|---|
With water; sodium hydroxide for 18h; | 66% |
(3S,3aS,4S,4aS,6S,8aR,8bR,11S)-6,11-dihydroxy-3-methyl-12-methylene-2-oxo-4a,6-ethano-3,8b-prop-1-enoperhydroindeno[1,2-b]furan-4-carboxylic acid
2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide
Conditions | Yield |
---|---|
With Celite; silver carbonate In dichloromethane Heating; | 63% |
2,2,2-trifluorodiazoethane
(3S,3aS,4S,4aS,6S,8aR,8bR,11S)-6,11-dihydroxy-3-methyl-12-methylene-2-oxo-4a,6-ethano-3,8b-prop-1-enoperhydroindeno[1,2-b]furan-4-carboxylic acid
acetonitrile
Conditions | Yield |
---|---|
With copper(l) iodide In toluene at 25℃; for 12h; | 62% |
(3S,3aS,4S,4aS,6S,8aR,8bR,11S)-6,11-dihydroxy-3-methyl-12-methylene-2-oxo-4a,6-ethano-3,8b-prop-1-enoperhydroindeno[1,2-b]furan-4-carboxylic acid
1-bromo-1-deoxy-2,3,4,6-tetra-O-acetyl-a-D-galactopyranoside
Conditions | Yield |
---|---|
With Celite; silver carbonate In dichloromethane Heating; | 61% |
(3S,3aS,4S,4aS,6S,8aR,8bR,11S)-6,11-dihydroxy-3-methyl-12-methylene-2-oxo-4a,6-ethano-3,8b-prop-1-enoperhydroindeno[1,2-b]furan-4-carboxylic acid
acetobromocellobiose
Gibberellin A3 heptaacetylcellobiosylester
Conditions | Yield |
---|---|
With triethylamine In acetone for 16h; Ambient temperature; | 52% |
(3S,3aS,4S,4aS,6S,8aR,8bR,11S)-6,11-dihydroxy-3-methyl-12-methylene-2-oxo-4a,6-ethano-3,8b-prop-1-enoperhydroindeno[1,2-b]furan-4-carboxylic acid
1-bromo-2,3,4-tri-O-acetyl-α-D-xylopyranose
Conditions | Yield |
---|---|
With Celite; silver carbonate In dichloromethane Heating; | 48% |
(3S,3aS,4S,4aS,6S,8aR,8bR,11S)-6,11-dihydroxy-3-methyl-12-methylene-2-oxo-4a,6-ethano-3,8b-prop-1-enoperhydroindeno[1,2-b]furan-4-carboxylic acid
Epigibberic acid
Conditions | Yield |
---|---|
With hydrogenchloride; water Wagner-Meerwein Rearrangement; Reflux; | 38% |
With hydrogenchloride Heating; |
(3S,3aS,4S,4aS,6S,8aR,8bR,11S)-6,11-dihydroxy-3-methyl-12-methylene-2-oxo-4a,6-ethano-3,8b-prop-1-enoperhydroindeno[1,2-b]furan-4-carboxylic acid
Conditions | Yield |
---|---|
With triethylamine In ethanol at 20℃; | 35% |
Empirical Formula: C19H22O6
Molecular Weight: 346.3744
EINECS: 201-001-0
Structure of Gibberellic Acid (CAS NO.77-06-5):
Index of Refraction: 1.661
Molar Refractivity: 85.786 cm3
Molar Volume: 231.972 cm3
Polarizability: 34.008 10-24cm3
Surface Tension: 71.863 dyne/cm
Density: 1.493 g/cm3
Flash Point: 231.438 °C
Enthalpy of Vaporization: 106.599 kJ/mol
Melting Point: 227 °C
Boiling Point: 628.595 °C at 760 mmHg
Vapour Pressure: 0 mmHg at 25°C
Storage temp: 0-6°C
Water Solubility: 5 g/L (20 º C)
Stability: Stable. Combustible. Incompatible with acids, strong oxidizing agents.
Product Categories: FINE Chemical & INTERMEDIATES; Plant Oils, Toxins, Phenolic Acids & Derivatives; Biochemistry; Plant Growth Regulators; Plant Growth Trgulators (Others); Antibiotic Explorer
Synonyms of Gibberellic Acid (CAS NO.77-06-5): (1alpha,2beta,4aalpha,4bbeta,10beta)-2,4a,7-Trihydroxy-1-methyl-8-methylenegibb-3-ene-1,10-dicarboxylic acid 1,4a-lactone ; (3S,3aR,4S,4aS,7S,9aR,9bR,12S)-7,12-Dihydroxy-3-methyl-6-
methylene-2-oxoperhydro-4a,7-methano-9b,3-propenoazuleno(1,2-b)furan-4-carboxylic acid ; Activol ; Berelex ; Brellin ; CCRIS 4820 ; Caswell No. 467 ; Cekugib ; Gibberellin ; Gibberellin A3 ; Gibefol ; Gibrescol ; Gibreskol ; Grocel ; Pro-Gibb Plus ; Regulex ; Ryzup
Gibberellic acid has the main following uses:
1.Gibberellic acid is a very potent hormone whose natural occurrence in plants controls their development. Since Gibberellic acid regulates growth, applications of very low concentrations can have a profound effect while too much will have the opposite effect. It is usually used in concentrations between 0.01-10 mg/L.
2.Gibberellic acid is a simple gibberellin, promoting growth and elongation of cells.
3.Gibberellic acid is sometimes used in laboratory and greenhouse settings to trigger germination in seeds that would otherwise remain dormant. It is also widely used in the grape-growing industry as a hormone to induce the production of larger bundles and bigger grapes, especially Thompson seedless grapes, and in the Okanagan and Creston Valley it is used in the cherry industry as a growth regulator.
1. | dnd-sal:spr 1 mmol/L | PYTCAS Phytochemistry. An International Journal of Plant Biochemistry. 11 (1972),3135. | ||
2. | dnd-mam:lym 1 mmol/L | PYTCAS Phytochemistry. An International Journal of Plant Biochemistry. 11 (1972),3135. | ||
3. | orl-mus TDLo:142 g/kg/78W-I:ETA | NTIS** National Technical Information Service. (Springfield, VA 22161) (Formerly U.S. Clearinghouse for Scientific and Technical Information) PB223-159 . | ||
4. | orl-rat LD50:6300 mg/kg | 85ARAE Agricultural Chemicals, Books I, II, III, and IV. 3 (1976/77),43. |
EPA Genetic Toxicology Program. Reported in EPA TSCA Inventory.
Hazard Codes: Xi
Risk Statements: 36
R36:Irritating to eyes.
Safety Statements: 26-36
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S36:Wear suitable protective clothing.
WGK Germany: 3
RTECS: LY8990000
F: 10
HS Code: 29322980
Hazardous Substances Data 77-06-5(Hazardous Substances Data)
Mildly toxic by ingestion of gibberellic acid . It is showed to be questionable carcinogen by experimental tumorigenic data. When heated to decomposition it emits acrid smoke and irritating fumes.
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